Cyanogen Bromide → HCID 19874480, compound

HRID 465464Notes

Reaction equation

HRID 465464 reaction equation
[N:1]#[C:2]Br.[CH2:4]([C:8]1[CH:19]=[CH:18][C:11]([O:12][CH2:13][CH:14]([OH:17])[CH2:15][NH2:16])=[CH:10][CH:9]=1)[C:5]([CH3:7])=[O:6].C([O-])(=O)C.[Na+]>CO.Cl>[NH2:1][C:2]1[O:17][CH:14]([CH2:13][O:12][C:11]2[CH:18]=[CH:19][C:8]([CH2:4][C:5]([CH3:7])=[O:6])=[CH:9][CH:10]=2)[CH2:15][N:16]=1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 19874539HCID 19874539, compound

Product 1

HCID 19874480HCID 19874480, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent3×

Procedure

A solution of cyanogen bromide (0.88 g) in methanol (100 ml) was added, dropwise, to a stirred solution of (4-acetonylphenoxy)-3-amino propan-2-ol), ethylene ketal (3.62 g) and sodium acetate (1.46 g) in methanol (30 ml). The reaction mixture was stirred at ambient temperature for 20 hr. evaporated, cooled in ice, diluted with 2N sodium hydroxide solution and extrated into chloroform. The organic layer was dried (MgSO4) and evaporated to an oil which was purified by column chromatography on silica gel. Elution with acetonitrile/methanol/ammonia (15:2:1) gave a low-melting solid which was dissolved in a mixture of methanol (30 ml) and 2N hydrochloric acid (30 ml) and stirred at ambient temperature for 4 hr. The methanol was evaporated and the aqueous residue was basified by addition of 2N sodium hydroxide solution, extracted into chloroform, dried (MgSO4) and evaporated to give 2-amino-5-(4-acetonylphenoxymethyl]-4,5-dihydrooxazole.

Workup

  1. customevaporated
  2. temperaturecooled in ice
  3. additiondiluted with 2N sodium hydroxide solution
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated to an oil which
  6. customwas purified by column chromatography on silica gel
  7. washElution with acetonitrile/methanol/ammonia (15:2:1)
  8. customgave a low-melting solid which
  9. stirringstirred at ambient temperature for 4 hr
  10. customThe methanol was evaporated
  11. additionthe aqueous residue was basified by addition of 2N sodium hydroxide solution
  12. extractionextracted into chloroform
  13. dry with materialdried (MgSO4)
  14. customevaporated

Sources & evidence

ORD record
ord-7a2d85b000384420ad68e1e0a1691c6d
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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